Monoazo dyestuffs of the pyrazolone series able to be chromated and process of making same.



I EMIL WEBER, OE EASEE, SWITZERLAND, ASSIGNOE T SOCIETY OF CHEMICAL INDUSTRY IN BASEE, @IIF EASEL, SWITZERLAND.

MONQMO JDYESTUIEIFS THE PTJRIAZOLONE SERIES AEEE TO BE CHROMATEID AND PROCESS OF MAKING SAME.

newness.

Ito Drawing.

To all whom it may concern:

Be it known that T, EMIL JREBER, chemist, a citizen of the Swiss Republic, and resident of Basel, Switzerland, have invented new and useful Monoazo Dyestufis of the Pyrazolone Series Able to be Chromated and Process of Making Same, of which the followin is a full, clear, and exact specification.

n the U. S. Letters Patent No. 1210808 is described a process for the manufacture of monoazodyestufis of the pyrazolone series, able to be chromated, consisting in combining the diazoderivative of orthoaminophenol or of aminonaphthols or of their derivatives with pyrazolone derivatives of the benzene or the naphthalene series containing a hydroxyl group in the aryl radical.

T have now found that monoazodyestufis of the pyrazolone series capable of being chromated, can also be obtained by combining the diazoderivative of the anthranilic acid or of its derivatives with the said pyrazolone derivatives. The new dyestufls thus obtained are distinguished from those of the above specified U. S. LetterslPatent by their more yellow tints.

The sodium salt of the new dystufis are yellow to orange-brown powders soluble in water with greenish-yellow to orange-yellow coloration. They are insoluble or di cultly soluble in alcohol and soluble in concentrated sulfuric acid with greenish-yellow to orange-red coloration. They dye wool in' an acid bath yellow to orange tints. The subsequently chromated tints are yellow, orange to red-brown and are fast to light, fulling and, potting.

The process is illustrated by the following examples Example 1: i A solution of the diazoderivative of 13.7 parts of anthranilic acid and a solution of 31.5 parts of 1- (5-sulfo-3- carboXy-2-oxy) -phen l-3-methyl 5 pyrazolone (prepared by t e condensation of 5- sulfo 3-carboxy 2 ox 1 hydrazinobenzene with acetoacetic ether; made alkaline by so- .dium carbonate are poured together. The

yellow monoazodyestuff thus produced is separated in the .usual manner by addition of common salt. It constitutes in a dry state an orange-yellow powder, dyes wool in an acid bath gold-yellow tints turning, when subsequently chromated, to a light brownishyellow fast to fulling and to potting.

Specification of Letters Patent.-

tPatented June 25, TQM.

.Applicatjlonfiled September 11, 1917. -Serial1to. 190,720.

Example 2: By substituting in the foregoing Example 1 for the pyrazolone derivative indicated 32 parts of the pyrazolone of the 2 amino 5 oxy naphthalene-7-sulfonie acld, an orange-red dyestufi' is obtained which dyes wool in an acid bath bright orange tints turning, when subsequently chromated, to a red-brown fast to fulling,

1i ht and potting. v

xample '3: The diazosolution derived from 17.1 arts of chloroanthranilic acid (NH :COO :Cl= 1:2 :4) is added to a solution of 30.5 arts of 1 (5-chlor-3-sulfo-2- oxy) -pheny -3-methyl-5.-pyrazolone (obtained by condensation of 5-chlor-3-sulfo-2- oxy-l-hydrazinobenzene with acetoacetic ether) made alkaline by sodium carbonate. ,The combmati'on achieved, the dyestufi' is separated by addition of common salt in the form of a yellow precipitate. It dyes wool in an acid bath yellow tints turning, when subsequently chromated, to a deep yellow fastto fulling, light and potting.

Exam 1e 4: 21 parts of sulfoanchranilic acid (N :CO()1][*I:E3(),H=1:2 :5) are diazotized in the usual manner and the resulting diazoderivative is poured in a solution of 23.5 parts of 1-(5 -nitro-2'-oxy)-phenyl-3- methyl-5-pyrazolone made alkaline by sodium carbonate.

The dyestufi separated in the usual manner, after the combination is achieved, constitutes in a dry state an orange-brown powder and dyes wool in an acid bath yellow pure tints turning, when subse uently chromated, to a brownish yellow f ast to light, fulling and potting.

A similar dystufi' of excellent fastness to tulling and potting is obtained, if in the foregoing example 23.4 parts ofl-( F-oxy- 3'carboxy) -phenyl 3 methjyl 5 pyrazolone are employed instead of the- 23.5 arts of 1- (5'-mtro-2-oxy) -phenyl-3- methy 5 pyrazolone.

What I claim is:

1. The herein described process for the manufacture of monoazodyestufls of the pyrazolone series consisting in combining the diazoderivative of an anthranilic compound with an oxyaryl substituted pyrazolone. I

2. As new products, the herein described monoazodyestuds of the pyrazolone series,

, being combination products of diazoderivatives of anthranilic compounds with oxyaryl substituted pyrazolones and the sodium salts of which constitute yellow to orange-brown powders, soluble in water with greenishyellow to orange-yellow coloration and difficulty soluble to insoluble in alcohol and soluble in concentrated sulfuric acid with greenish-yellow to orange-red coloration and dyeing wool in an acid bath yellow to orange tints turning, when subsequently chromated,

,to yellow, orange and red-brown tints fast to light, fulling and potting.

3. As a new article of manufacture, the herein described dyestufi being the combination product of the diazoderivative of anthranilic acid with 1- (5 '-sulfo-3'-carboxy- 

